Controlled syntheses of 12-oxo-PDA and its 13-epimer

Kobayashi, Yuichi; Matsuumi, Michitaka

doi:10.1016/s0040-4039(02)00786-4

Cited by 15 publications

(14 citation statements)

References 25 publications

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“…These data were consistent with those of derivatives of oxophytodienoic acid (Bohlmann et al, 1982(Bohlmann et al, , 1983. The data of H9 and H13 were largely consistent with those published for 12-oxo-cis-10,15-phytodienoic acid and its methyl ester (Ainai et al, 2003;Baertschi et al, 1988;Crombie and Mistry, 1991;Kobayashi and Matsuumi, 2002) (compounds 3 and 4), and for 12-oxo-trans-10,15-phytodienoic acid and its methyl ester (compounds 1 and 2), respectively (Ainai et al, 2003;Baertschi et al, 1988;Bohlmann et al, 1982;Chu et al, 1995;Kobayashi and Matsuumi, 2002). Moreover, the signals of H10 and H11, i.e.…”

Section: Chemical Investigation Of the Secreted Materialssupporting

confidence: 89%

“…Moreover, the signals of H10 and H11, i.e. d H = 7.73 and 6.18 for compounds 3 and 4, and d H = 7.60 and 6.12 for 1 and 2 were consistent with literature data for 12-oxo-cis-phytodienoic acid and its stereoisomer (Ainai et al, 2003;Kobayashi and Matsuumi, 2002). The relative and absolute configurations at C9 and C13 of 1-4 were established in a next step.…”

Section: Chemical Investigation Of the Secreted Materialssupporting

confidence: 85%

“…oxylipins has been previously studied by stereoselective synthesis of 12-oxo-cyclopentenoic acid derivatives and comparison of their optical rotation. The [a] D values of (9S, 13S) stereoisomers were smaller than those of (9S, 13R) stereoisomers (Kobayashi and Matsuumi, 2002). Specific optical rotations for compounds 1-4 were +35.5, +29.9, +60.0, and +107.3, respectively.…”

Section: Chemical Investigation Of the Secreted Materialsmentioning

confidence: 93%

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Antibacterial compounds from Salvia adenophora Fernald (Lamiaceae)

et al. 2015

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Section: Chemical Investigation Of the Secreted Materialssupporting

confidence: 89%

Section: Chemical Investigation Of the Secreted Materialssupporting

confidence: 85%

Section: Chemical Investigation Of the Secreted Materialsmentioning

confidence: 93%

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Antibacterial compounds from Salvia adenophora Fernald (Lamiaceae)

et al. 2015

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“…The simplified synthetic pathway of 8-(4-oxocyclopentenyl)octanoic acid (8) was modified from that of 12-oxo-PDA given by Kobayashi & Matsuumi (2002) (Fig. 2b).…”

Section: Synthesis Of Cyclopentenone Compounds (8)mentioning

confidence: 99%

Synthetic molecular mimics of naturally occurring cyclopentenones exhibit antifungal activity towards pathogenic fungi

et al. 2011

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The naturally occurring reactive electrophilic species 12-oxo-phytodienoic acid (12-oxo-PDA) is a potent antifungal agent, whereas the plant growth regulator jasmonic acid, which is synthesized from 12-oxo-PDA, is ineffective. To address what structural features of the molecule endow it with antifungal activity, we synthesized a series of molecular mimics of 12-oxo-PDA varying in the length of the alkyl chain at its C-4 ring position. The octyl analogue (4-octyl cyclopentenone) was the most effective at suppressing spore germination and subsequent mycelial growth of a range of fungal pathogens and was particularly effective against Cladosporium herbarum and Botrytis cinerea, with minimum fungicidal concentrations in the range 100-200 mM. Introduction of a carboxyl group to the end of the chain, mimicking natural fatty acids, markedly reduced antifungal efficacy. Electrolyte leakage, indicative of membrane perturbation, was evident in both C. herbarum and B. cinerea exposed to 4-octyl cyclopentenone. Lipid composition analysis of the fungal spores revealed that those species with a high oil content, namely Fusarium oxysporum and Alternaria brassicicola, were less sensitive to 4-octyl cyclopentenone. The comparable hydrophobicity of 4-octyl cyclopentenone and 12-oxo-PDA accounts for the similar spore suppression activity of these two compounds. The relative ease of synthesis of 4-octyl cyclopentenone makes it an attractive compound for potential use as an antifungal agent.

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“…Actually, we succeeded in stereoselective synthesis of 12-oxo-PDA, in which the two side chains are attached on the ring in a cis fashion. 5 We then became interested in the title reaction in order to expand the possibility of the reaction in organic synthesis. Herein, we report our results along this line.…”

Section: Introduction Of a Hydroxylmethyl Group Onto The Ring Of 4-cymentioning

confidence: 99%